Azo dyes from 1,3,4-thiadiazol-2-yl and 1,2,4-thiadiazol-5-yl moieties bearing sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on their rings

ABSTRACT

This invention relates to azo dyes in which the diazotized amino component bears sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on its ring. These dyes have excellent dyeing properties on polyamide fibers and also impart color to cellulose acetate fibers and wool. 
     The dyes correspond to the general formulae: ##STR1## wherein X&#39; is O, NH, N(alkyl)-- or N(aryl)--; Z is selected from straight- or branched-chain alkylene which may be substituted, for example, with phenyl, halogen, OSO 3  M, alkoxy, aryloxy and the like; M is H, Na, K or NH 4  ; and the coupler C is selected from those of the formulae ##STR2## wherein the R substituents are selected from a wide variety of groups known to the art.

This invention concerns novel dyes in which the diazo moieties contain sulfate groups. These dyes are substantially water soluble and are particularly useful for dyeing polyamide, wool and the like, and exhibit excellent properties, including fastness to light and dyeability.

The dyes of this invention correspond to the general formula: ##STR3## wherein D is a 1,3,4-thiadiazol-2-yl or 1,2,4-thiadiazol-5-yl radical; C is the coupler portion of the molecule; X' is O, NH, N(alkyl)--, or N(aryl)--; Z is selected from straight- or branched-chain alkylene, which may be substituted, for example, with phenyl, halogen, OSO₃ M, alkoxy or aryloxy groups, --CH₂ (CH₂)_(m) V--CH₂ (CH₂)_(p) --, where m is 1, 2 or 3, p is 0, 1, 2 or 3, and V is O, S, SO₂, --SO₂ NH--, --SO₂ N(alkyl)--, SO₂ N(aryl)--N(SO₂ aryl)--, --NH, --NHCO--, --NHCONH, --N(SO₂ alkyl), or --CON(alkyl); and M is H, Na, K or NH₄.

More particularly, the dyes correspond to the formula above wherein D represents the radicals ##STR4## and the coupler C is selected from ##STR5## wherein R² and R¹⁴ each represents up to three groups selected from hydrogen, fluorine, chlorine, bromine, alkyl, cycloalkyl, alkoxy, phenoxy, alkylthio, arylthio, and radicals having the formula --NH--X--R³ in which X is --CO--, --COO--, or --SO₂ -- and R³ is selected from alkyl and alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy, and when X is --CO--, R³ also is selected from hydrogen, amino, alkylamino, alkylcarbamoyl, dialkylamino, arylamino, aryl, and furyl;

R⁴ and R⁵ are each selected from hydrogen, alkyl, aryl, cycloalkyl, R⁴ and R⁵ represent a single, combined group --CH₂ CH₂ CH₂ CH₂ CH₂ --, --CH₂ CH₂ OCH₂ CH₂ --, --CH₂ CH₂ --S--CH₂ CH₂ --, --CH₂ CH₂ --SO₂ --CH₂ CH₂ -- and --CH₂ CH₂ --R¹⁵ --CH₂ CH₂ -- wherein R¹⁵ is alkyl, aryl, cycloalkyl or alkanoyl, and alkyl substituted with halogen, CN, OH, alkoxy, aryloxy, alkoxyalkoxy alkanoyl, alkanoyloxy, carbamoyl, alkylcarbamoyl, sulfamoyl, alkylsulfamoyl, alkoxyalkanoyloxy, and cycloalkyl;

R⁸ is one or two groups each selected from hydrogen, alkyl and alkyl substituted with --CN, alkoxy, alkoxycarbonyl, alkoxycarbonyloxy, phenyl, cyclohexoxy, --OH, --Cl and Br;

R⁹, R¹⁰ and R¹¹ are each selected from hydrogen, alkyl, phenyl, or phenyl substituted with 1-3 groups selected from Cl, Br, alkyl or alkoxy, alkylthio, benzylthio, cyclohexylthio, phenylthio, and substituted phenylthio;

Q and Q' are each selected from --CO--, --SO₂ --, or --CN; R¹² and R¹³ are each selected from alkyl, hydroxyalkyl, alkoxy, alkoxycarbonylamino, trifluoromethyl, phenyl or phenyl substituted with 1-3 groups selected from Cl, Br, alkyl or alkoxy, alkoxycarbonylalkyl, cyanolalkyl, amino, haloalkyl, alkylamino, alkylthio, benzylthio, cyclohexylthio, phenylthio, substituted phenylthio, phenyl substituted phenyl, benzyl, alkanoylamino, alkylsulfonamido, alkylcarboxamido, benzamido and alkoxycarbonylalkylthio; R¹² and R¹³ may combine to form an alkylene bridge of 3 to 5 carbons, or to form an arylene or cycloalkylene radical of 5-6 carbons connecting Q and Q'; R¹⁶ and R¹⁷ are selected from hydrogen, cycloalkyl, aryl, alkyl, and alkyl substituted with alkoxy, hydroxy, alkoxyalkoxy, hydroxyalkoxy, carbamoyl, sulfamoyl, acylamido, or alkenylsulfonyl, and aryl substituted with hydroxyalkyl; e is 1 or 2; and t and t' are each 1 or zero. It is noted that when t or t' is zero, the corresponding Q or Q' group is --CN;

Each of the aliphatic portions of the above alkyl, cycloaliphatic, alkoxy, aryl, aryloxy alkanoyl and the like groups, as well as the aryl and aryloxy groups, may be substituted further with up to three of the following: hydroxy; halogen; cyano; succinimido; glutarimido; phthalimido; 2-pyrrolidono; cyclohexyl; phenyl or phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl; alkanoylamino; sulfamoyl; alkylsulfamoyl; vinylsulfonyl; acrylamido, phthalimidinyl; benzoylsulfonicimidyl; alkylsulfonamido; phenylsulfonamido; alkoxycarbonylamino; alkylcarbamoyloxy; alkoxycarbonyl; alkoxycarbonyloxy; ##STR6## wherein Y is --NH--, --NH--alkyl--, --O--, --S--, or --CH₂ O--; --S--R⁶ wherein R⁶ here and above is alkyl, phenyl, phenyl substituted with halogen, alkyl, alkoxy, alkanoylamino, cyano, or alkoxycarbonyl, pyridyl, pyrimidinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, triazolyl, or ##STR7## --SO₂ R³ ; --COOR³ ; --OXR³ ; --NH--X--R³ ; --X--R³ ; --OCO--R³ ; --CONR⁷ R⁷ ; --SO₂ NR⁷ R⁷ ; wherein R³ and X are as defined above and each R⁷ is selected from H and R³ ; alkoxy; alkoxy substituted with hydroxy, cyano, alkanoyloxy, or alkoxy; phenoxy or phenoxy substituted with one or more of alkyl, alkoxy or halogen. All of the aliphatic portions of the various groups herein contain from 1-6 carbons, and are straight or branched chain.

The dyes of this invention impart yellow to blue shades on fibers, particularly polyamides, and are especially useful for dyeing polyamide (nylon) carpets, giving good fastness to light, azone, oxides of nitrogen, washing, sublimation, crocking and the like, and having good leveling, transfer, exhaustion, and build properties.

The couplers used in this invention are prepared according to known procedures. The dyes may be prepared by reacting the coupler with a diazonium salt which contains one or two carbalkoxy groups. The product is reacted first with an aminoalcohol H--X'--Z--OH (X' is NH, Z is alkylene) to convert to a N-(hydroxyalkyl)carbamyl group, or with an alkanediol H--X'--Z--OH (X' is O, Z is alkylene) to convert to a hydroxyalkoxycarbonyl group. Subsequently, the material is reacted with concentrated sulfuric acid to form the sulfate ester: ##STR8##

Alternatively, a diazotizable amine containing a hydroxyalkoxycarbonyl group or a N-(hydroxyalkyl)carbamyl group may be sulfated before diazotization and coupling: ##STR9##

This invention will be further illustrated by the following examples although it will be understood that these examples are included merely for purposes of illustration and are not intended to limit the scope of the invention. The compounds listed in the tables below can be prepared by procedures analogous to those described above.

                                      TABLE I                                      __________________________________________________________________________      ##STR10##                                                                     R.sup.2    R.sup.4 R.sup.5   X'Z         M                                     __________________________________________________________________________     2-CH.sub.3, 5-NHCOCH.sub.3                                                                H       C.sub.2 H.sub.5                                                                          NHC.sub.2 H.sub.4                                                                          Na                                    H          C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 N(COCH.sub.3).sub.2                                                      N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                                     3-CH.sub.3 C.sub.2 H.sub.4 Cl                                                                     C.sub.2 H.sub.4 CN                                                                       NHC.sub.2 H.sub.4                                                                          K                                     "          "       "         NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                                     3-CH.sub.3 C.sub.2 H.sub.4 OH                                                                     C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           Na                                    3-NHCOCH.sub.3                                                                            C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 CN                                                                       NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                                    2-OCH.sub.3, 5-NHCOCH.sub.3                                                               C.sub. 2 H.sub.4 OCOCH.sub.3                                                           C.sub.2 H.sub.4 OCOCH.sub.3                                                              NHC.sub.2 H.sub.4                                                                          NH.sub.4                              3-Cl       C.sub.2 H.sub.4 OH                                                                     C.sub.6 H.sub.13                                                                         OC.sub.2 H.sub.4                                                                           K                                     2-Cl       H       C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           K                                     2-CH.sub.3, 3-Cl                                                                          H       CH.sub.2 C.sub.6 H.sub.5                                                                 NHC.sub.3 H.sub.6                                                                          K                                     H          C.sub.2 H.sub.4 OH                                                                     C.sub.2 H.sub.4 CN                                                                       OC.sub.2 H.sub.4                                                                           NH.sub.4                              H          C.sub.2 H.sub.4 OSO.sub.3 K                                                            C.sub.2 H.sub.5                                                                          NHC.sub.2 H.sub.4                                                                          K                                     3-CH.sub.3 C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "           "                                     3-NHCOCH.sub.3                                                                            "       C.sub.2 H.sub.4 CONH.sub.2                                                               "           "                                     H          "       C.sub.2 H.sub.4 NHCOCH.sub.3                                                             N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          Na                                    "          "       H         NHC.sub.2 H.sub.4                                 H          CH.sub.2 CH.sub.2OCH.sub.2 CH.sub.2                                                              NHC.sub.2 H.sub.4                                                                          Na                                    H          CH.sub.2 CH.sub.2SCH.sub.2 CH.sub.2                                                              NHC.sub.2 H.sub.4                                                                          Na                                    H          CH.sub.2 CH.sub.2SO.sub.2CH.sub.2 CH.sub. 2                                                      NHC.sub.2 H.sub.4                                                                          Na                                    H          CH.sub.2 CH.sub.2NHCH.sub.2 CH.sub.2                                                             NHC.sub.2 H.sub.4                                                                          Na                                    H          CH.sub.2 CH.sub.2NCOCH.sub.3CH.sub.2 CH.sub.2                                                    NHC.sub.2 H.sub.4                                                                          Na                                    3-CH.sub.3 H       C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                        NHC.sub.2 H.sub.4                                                                          Na                                    2-OC.sub.6 H.sub.5                                                                        C.sub.2 H.sub.4 CN                                                                     C.sub.2 H.sub.4 N(COCH.sub.3).sub.2                                                      "           "                                     2-SCH.sub.3                                                                               C.sub.2 H.sub.4 OCOCH.sub.3                                                            C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5                                               NHC.sub.2 H.sub.4                                                                          K                                     3-SC.sub.6 H.sub.5                                                                        CONH.sub.2                                                                             C.sub.2 H.sub.4 SO.sub.2 NH(C.sub.2 H.sub.5)                                             NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                                     3-NHCOOCH.sub.3                                                                           C.sub.2 H.sub.4 OH                                                                     C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           Na                                    3-NHSO.sub.2 CH.sub.3                                                                     C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 CN                                                                       NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                                    2-OCH.sub.3, 5-NHCOCH.sub.3                                                               C.sub.2 H.sub.4 OCOCH.sub.3                                                            C.sub.2 H.sub.4 OCOCH.sub.3                                                              NHC.sub.2 H.sub.4                                                                          NH.sub.4                              3-NHCOCH.sub.2 Cl                                                                         C.sub.2 H.sub.4 OH                                                                     C.sub.6 H.sub.13                                                                         OC.sub.2 H.sub.4                                                                           K                                     3-NHCOC.sub.2 H.sub.4 OH                                                                  H       C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           K                                     2-CH.sub.3, 3-Cl                                                                          H       CH.sub.2 C.sub.6 H.sub.5                                                                 NHC.sub.3 H.sub.6                                                                          K                                     2-NHCONHC.sub.2 H.sub.5                                                                   C.sub.2 H.sub.4 OH                                                                     C.sub.2 H.sub.4 CN                                                                       OC.sub.2 H.sub.4                                                                           NH.sub.4                              2-NHCON(C.sub.2 H.sub.5).sub.2                                                            C.sub.2 H.sub.4 OSO.sub.3 K                                                            C.sub.2 H.sub.5                                                                          NHC.sub.2 H.sub.4                                                                          K                                     3-CH.sub.3 C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "           "                                     3-NHCOCH.sub.3                                                                            "       C.sub.2 H.sub.4 CONH.sub.2                                                               "           "                                     H          "       C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "           Na                                    __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________      ##STR11##                                                                     R.sup.2   R.sup.8                                                                               R.sup.4   X'Z         M                                       __________________________________________________________________________     7-CH.sub.3                                                                               2-CH.sub.3                                                                            C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           Na                                      7-CH.sub.3                                                                               2-CH.sub.3                                                                            C.sub.2 H.sub.4 OSO.sub.3 K                                                              NHC.sub.2 H.sub.4                                                                          K                                       H         H      C.sub.2 H.sub.4 OC.sub.6 H.sub.11                                                        OC.sub.2 H.sub.4                                                                           Na                                      5-CH.sub.3                                                                               H      C.sub.4 H.sub.9                                                                          NHC.sub.2 H.sub.4                                                                          Na                                      7-CH.sub.3                                                                               2-CH.sub.3                                                                            C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "           "                                       7-CH.sub.3                                                                               2,2,4-(CH.sub.3).sub.3                                                                "         N(C.sub.2 H.sub.5)C.sub.2 H.sub.4                                                          "                                       8-CH.sub.3                                                                               H      C.sub.2 H.sub.4 Cl                                                                       OC.sub.2 H.sub.4                                                                           NH.sub.4                                H         2,2,4-(CH.sub.3).sub.3                                                                C.sub.2 H.sub.4 OCH.sub.3                                                                OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          K                                       7-NHCOCH.sub.3                                                                           "      C.sub.2 H.sub.4 Br                                                                       NHC.sub.2 H.sub.4                                                                          K                                       "         5-CH.sub.3                                                                            CH.sub.2 CHOHCH.sub.2 OH                                                                 OC.sub.2 H.sub.4                                                                           K                                       7-CH.sub.3                                                                               2-CH.sub.3                                                                            CH.sub.3  NHC.sub.2 H.sub.4                                                                          K                                       7-C.sub.6 H.sub.11                                                                       3-OH   C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                        NHC.sub.2 H.sub.4                                                                          Na                                      7-OC.sub.6 H.sub.5                                                                       3-CN   C.sub.2 H.sub.4 N(COCH.sub.3).sub.2                                                      N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                                       7-SCH.sub.3                                                                              3-OCOCH.sub.3                                                                         C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5                                               NHC.sub.2 H.sub.4                                                                          K                                       7-SC.sub.6 H.sub.5                                                                       2-CH.sub.3                                                                            C.sub.2 H.sub.4 SO.sub.2 NH(C.sub.2 H.sub.5)                                             NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                                       7-NHCOOCH.sub.3                                                                          "      C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           Na                                      7-NHSO.sub.2 CH.sub.3                                                                    2-C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.4 CN                                                                       NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                                      7-OCH.sub.3                                                                              3-OCOCH.sub.3                                                                         C.sub.2 H.sub.4 OCOCH.sub.3                                                              NHC.sub.2 H.sub.4                                                                          NH.sub.4                                7-NHCOCH.sub. 2 Cl                                                                       3-OH   C.sub.6 H.sub.13                                                                         OC.sub.2 H.sub.4                                                                           K                                       7-NHCOC.sub.2 H.sub.4 OH                                                                 3-CONH.sub.2                                                                          C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           K                                       7-CH.sub.3, 5-Cl                                                                         3-Cl   CH.sub.2 C.sub.6 H.sub.5                                                                 NHC.sub.3 H.sub.6                                                                          K                                       7-NHCONHC.sub.2 H.sub.5                                                                  3-OC.sub.6 H.sub.5                                                                    C.sub.2 H.sub.4 CN                                                                       OC.sub.2 H.sub.4                                                                           NH.sub.4                                7-NHCON(C.sub.2 H.sub.5).sub.2                                                           3-OC.sub.6 H.sub.5                                                                    C.sub.2 H.sub.5                                                                          NHC.sub.2 H.sub.4                                                                          K                                       7-CH.sub.3                                                                               3-SC.sub.2 H.sub.5                                                                    C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "           "                                       7-NHCOCH.sub.3                                                                           3-CONHC.sub.2 H.sub.5                                                                 C.sub.2 H.sub.4 CONH.sub.2                                                               "           "                                       H         3-OCH.sub.3                                                                           C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "           Na                                      __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________      ##STR12##                                                                     R.sup.2   R.sup.8 R.sup.4   X'Z         M                                      __________________________________________________________________________     6-NHCOCH.sub.3                                                                           3-CH.sub.3                                                                             C.sub.2 H.sub.5                                                                          NHC.sub.2 H.sub.4                                                                          Na                                     6-CH.sub.3                                                                               3-CH.sub.3                                                                             C.sub.2 H.sub.5                                                                          OC.sub.2 H.sub.4                                                                           Na                                     6-Cl      "       C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           K                                      6-Br      2,3-di-CH.sub.3                                                                        C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                        "           NH.sub.4                               6-F       3-CH.sub.3                                                                             "         NHC.sub.2 H.sub.4                                                                          K                                      H         2-CH.sub.2 OH                                                                          CH(CH.sub.3).sub.2                                                                       "           "                                      H         2-CH.sub.2 OH                                                                          "         N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                                      6-NHCOCH.sub.3                                                                           2-CH.sub.2 Cl                                                                          C.sub.2 H.sub.5                                                                          NHC.sub.3 H.sub.6                                                                          Na                                     "         3-CH(CH.sub.3).sub.2                                                                   C.sub.2 H.sub.4 OCH.sub.3                                                                NHC.sub.2 H.sub.4                                                                          Na                                     6-CH.sub.3                                                                               3-CH.sub.3                                                                             "         "           Na                                     6-C.sub.6 H.sub.11                                                                       2-CH.sub.2 OC.sub.6 H.sub.5                                                            C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                        NHC.sub.2 H.sub.4                                                                          Na                                     6-OC.sub.6 H.sub.5                                                                       2-CH.sub.2 OC.sub.2 H.sub.5                                                            C.sub.2 H.sub.4 N(COCH.sub.3).sub.2                                                      "           "                                      6-SCH.sub.3                                                                               ##STR13##                                                                             C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5                                               NHC.sub.2 H.sub.4                                                                          K                                      6-SC.sub.6 H.sub.5                                                                       2-CH.sub.2 Cl                                                                          C.sub.2 H.sub.4 SO.sub.2 NH(C.sub.2 H.sub.5)                                             NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                                      6-NHCOOCH.sub.3                                                                          2-CH.sub.2 OH                                                                          C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           Na                                     6-NHSO.sub.2 CH.sub.3                                                                    "       C.sub.2 H.sub.4 CN                                                                       NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                                     8-OCH.sub.3,  5-NHCOCH.sub.3                                                              ##STR14##                                                                             C.sub.2 H.sub.4 OCOCH.sub.3                                                              NHC.sub.2 H.sub.4                                                                          NH.sub.4                               6-NHCOCH.sub.2 Cl                                                                        "       C.sub.6 H.sub.13                                                                         OC.sub.2 H.sub.4                                                                           K                                      6-NHCOC.sub.2 H.sub.4 OH                                                                 3-C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           K                                      8-CH.sub.3, 5-Cl                                                                         "       CH.sub.2 C.sub.6 H.sub.5                                                                 NHC.sub.3 H.sub.6                                                                          K                                      6-NHCONHC.sub.2 H.sub.5                                                                  2-CH.sub.2 OC.sub.6 H.sub.5                                                            C.sub.2 H.sub.4 CN                                                                       OC.sub.2 H.sub.4                                                                           NH.sub.4                               6-NHCON(C.sub.2 H.sub.5).sub.2                                                           2-CH.sub.2 OC.sub.6 H.sub.5                                                            C.sub.2 H.sub.5                                                                          NHC.sub.2 H.sub.4                                                                          K                                      6-OC.sub.6 H.sub.5                                                                       H       C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "           "                                      6-NHCOCH.sub.3                                                                           "       C.sub.2 H.sub.4 CONH.sub.2                                                               "           "                                      H         "       C.sub.2 H.sub.4 NHCOCH.sub.3                                                             N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          Na                                     __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________      ##STR15##                                                                     R.sup.9  R.sup.2   R.sup.4   X'Z         M                                     __________________________________________________________________________     C.sub.6 H.sub.5                                                                         H         CH.sub.3  NHC.sub.2 H.sub.4                                                                          Na                                    CH.sub.3 6-CH.sub.3                                                                               CH.sub.3  "           "                                     "        "         C.sub.6 H.sub.5                                                                          "           "                                     "        H         C.sub.2 H.sub.5                                                                          "           "                                     C.sub.6 H.sub.5                                                                         H         H         "           "                                     "        "         CH.sub.3  "           "                                     CH.sub.3 "         CH.sub.3  N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                                     "        5-OC.sub.2 H.sub.5                                                                       "         NHC.sub.3 H.sub.6                                                                          "                                     CH.sub.3 "         H         NHC.sub.2 H.sub. 4                                                                         "                                     C.sub.6 H.sub.4p-Br                                                                     H         H         "           "                                     C.sub.6 H.sub.5                                                                         "         C.sub.2 H.sub.4 CONH.sub.2                                                               "           K                                     C.sub.6 H.sub.4p-OCH.sub.3                                                              "         C.sub.2 H.sub.4 CN                                                                       N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          K                                     "        5-C.sub.6 H.sub.11                                                                       C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                        NHC.sub.2 H.sub.4                                                                          "                                     C.sub.2 H.sub.4 CN                                                                      6-OC.sub.6 H.sub.5                                                                       C.sub.2 H.sub.4 N(COCH.sub.3).sub.2                                                      "           "                                     C.sub.2 H.sub.4 OCOCH.sub.3                                                             6-SCH.sub.3                                                                              C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5                                               NHC.sub.2 H.sub.4                                                                          K                                     CH.sub.3 6-SC.sub.6 H.sub.5                                                                       C.sub.2 H.sub.4 SO.sub.2 NH(C.sub.2 H.sub.5)                                             NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                                     "        6-NHCOOCH.sub.3                                                                          C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           Na                                    C.sub.3 H.sub.7                                                                         6-NHSO.sub.2 CH.sub.3                                                                    C.sub.2 H.sub.4 CN                                                                       NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                                    CH.sub.3 6-OCH.sub.3,                                                                             C.sub.2 H.sub.4 OCOCH.sub.3                                                              NHC.sub.2 H.sub.4                                                                          NH.sub.4                                        5-NHCOCH.sub.3                                                       C.sub.2 H.sub.5                                                                         6-NHCOCH.sub.2 Cl                                                                        C.sub.6 H.sub.13                                                                         OC.sub.2 H.sub.4                                                                           K                                     "        6-NHCOC.sub.2 H.sub.4 OH                                                                 C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           K                                     "        "         CH.sub.2 C.sub.6 H.sub.5                                                                 NHC.sub.3 H.sub.6                                                                          K                                     C.sub.2 H.sub.5                                                                         6-NHCONHC.sub.2 H.sub.5                                                                  C.sub.2 H.sub.4 CN                                                                       OC.sub.2 H.sub.4                                                                           NH.sub.4                              C.sub.6 H.sub.4p-OCH.sub.3                                                              6-NHCON(C.sub.2 H.sub.5).sub.2                                                           C.sub.2 H.sub.5                                                                          NHC.sub.2 H.sub.4                                                                          K                                     C.sub.2 H.sub.5                                                                         6-CH.sub.3                                                                               C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "           "                                     C.sub.2 H.sub.5                                                                         6-NHCOCH.sub.3                                                                           C.sub.2 H.sub.4 CONH.sub.2                                                               "           "                                     CH.sub.3 H         C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "           Na                                    "        "         C.sub.2 H.sub.4 Cl                                                                       "           "                                     C.sub.6 H.sub.4p-CH.sub.3                                                               6-OH      "         "           "                                     __________________________________________________________________________

                  TABLE 5                                                          ______________________________________                                          ##STR16##                                                                     R.sup.9   R.sup.10    X'Z             M                                        ______________________________________                                         C.sub.6 H.sub.5                                                                          H           NHC.sub.2 H.sub.4                                                                              Na                                       CH.sub.3  "           OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                              Na                                       CH.sub.3  H           OC.sub.2 H.sub.4                                                                               Na                                       CH.sub.3  C.sub.6 H.sub.5                                                                            NHC.sub.2 H.sub.4                                                                              Na                                       CH.sub.3  C.sub.6 H.sub.5                                                                            NHC.sub.3 H.sub.6                                                                              Na                                       C.sub.6 H.sub.5                                                                          CH.sub.3    NHC.sub.2 H.sub.4                                                                              Na                                       C.sub.6 H.sub.5                                                                          "           "               NH.sub.4                                 "         "           N(C.sub.2 H.sub.5)C.sub.2 H.sub.4                                                              "                                        CH.sub.3  H           NHC.sub.2 H.sub.4                                                                              K                                        "         H           NH (CH.sub.2).sub.5                                                                            K                                        C.sub.6 H.sub.4p-Br                                                                      "           OC.sub.2 H.sub.4                                                                               K                                        C.sub.6 H.sub.4p-OCH.sub.3                                                               "           OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                              K                                        "         Br          NHC.sub.2 H.sub.4                                                                              K                                        C.sub.2 H.sub.4 CN                                                                       Br          N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                              K                                        C.sub.2 H.sub.4 OCOCH.sub.3                                                              Br          NHC.sub.2 H.sub.4                                                                              K                                        CH.sub.3  C.sub.2 H.sub.5                                                                            NHCH.sub.2CH(C.sub.6 H.sub.5)                                                                  K                                        "         C.sub.2 H.sub.5                                                                            OC.sub.2 H.sub.4                                                                               K                                        C.sub.3 H.sub.7                                                                          C.sub.6 H.sub.5                                                                            NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                             K                                        CH.sub.3  "           NHC.sub.2 H.sub.4                                                                              K                                        C.sub.2 H.sub.5                                                                          C.sub.6 H .sub.4p-CH.sub.3                                                                 OC.sub.2 H.sub.4                                                                               K                                        "         H           OC.sub.2 H.sub.4                                                                               K                                        "         CONHC.sub.2 H.sub.5                                                                        NHC.sub.3 H.sub.6                                                                              K                                        C.sub.2 H.sub.5                                                                          CH.sub.3    OC.sub.2 H.sub.4                                                                               K                                        C.sub.6 H.sub.4p-OCH.sub.3                                                               C.sub.2 H.sub.5                                                                            NHC.sub.2 H.sub.4                                                                              K                                        C.sub.2 H.sub.5                                                                          SCN         "               K                                        C.sub.2 H.sub.5                                                                          CONH.sub.2  "               K                                        CH.sub.3  CH(CH.sub.3).sub.2                                                                         "               K                                        "         C.sub.6 H.sub.5                                                                            "               K                                        C.sub.6 H.sub.4p-CH.sub.3                                                                C.sub.2 H.sub.5                                                                            NHC.sub.2 H.sub.4 OCH.sub.2                                                                    K                                        ______________________________________                                    

                                      TABLE 6                                      __________________________________________________________________________      ##STR17##                                                                     R.sup.4  R.sup.11    X'Z          M                                            __________________________________________________________________________     H        CH.sub.3    NHC.sub.2 H.sub.4                                                                           K                                            H        C.sub.6 H.sub.4p-OCH.sub.3                                                                 "            "                                            H        CF.sub.3    "            "                                            H        COOC.sub.2 H.sub.5                                                                         "            "                                                      ##STR18##  "            Na                                           H        C.sub.6 H.sub.5                                                                            "            K                                            C.sub.6 H.sub.5                                                                         C.sub.6 H.sub.4p-Br                                                                        "            "                                            "        C(CH.sub.3).sub.3                                                                          "            "                                            "        C.sub.6 H.sub.11                                                                           "            Na                                           "        C.sub.6 H.sub.5                                                                            "            Na                                           C.sub.6 H.sub.5 SO.sub.2                                                                CH.sub.3    N(CH.sub.3)C.sub.2 H.sub.4                                                                  Na                                           C.sub.2 H.sub.5 SO.sub.2                                                                "           NHC.sub.2 H.sub.4                                                                           K                                             ##STR19##                                                                              "           N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                           K                                             ##STR20##                                                                              CH.sub.3    NHC.sub.2 H.sub.4                                                                           K                                            CH.sub.3 CONH.sub.2  NHCH.sub.2CH(C.sub.6 H.sub.5)                                                               K                                            C.sub.2 H.sub.4 OH                                                                      C.sub.2 H.sub.5                                                                            OC.sub.2 H.sub.4                                                                            K                                            C.sub.2 H.sub.4 CN                                                                      "           NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          K                                            C.sub.2 H.sub.4 OCOCH.sub.3                                                             "           NHC.sub.2 H.sub.4                                                                           K                                            C.sub.6 H.sub.11                                                                        CF.sub.3    OC.sub.2 H.sub.4                                                                            K                                            C.sub.2 H.sub.4 OH                                                                      C.sub.6 H.sub.4p-Cl                                                                        OC.sub.2 H.sub.4                                                                            K                                            CH.sub.2 C.sub.6 H.sub.5                                                                CONHC.sub.2 H.sub.5                                                                        NHC.sub.3 H.sub.6                                                                           K                                            C.sub.2 H.sub.4 CN                                                                      CH(CH.sub.3).sub.2                                                                         OC.sub.2 H.sub.4                                                                            K                                            C.sub.2 H.sub.5                                                                         "           NHC.sub.2 H.sub.4                                                                           K                                            C.sub.2 H.sub.4 NHCOCH.sub.3                                                            C.sub.2 H.sub.5                                                                            "            K                                            C.sub.2 H.sub.4 CONH.sub.2                                                              CH.sub.3    "            K                                            C.sub.2 H.sub.4 NHCOCH.sub. 3                                                           C.sub.2 H.sub.5                                                                            "            K                                            "        C.sub.6 H.sub.5                                                                            "            K                                            __________________________________________________________________________

                  TABLE 7                                                          ______________________________________                                          ##STR21##                                                                     Q    Q'     R.sup.12   R.sup.13   X'Z      M                                   ______________________________________                                         CO   CO     C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.5                                                                           NHC.sub.2 H.sub.4                                                                       Na                                  CO   CO     CH.sub.3   CH.sub.2 OH                                                                               "        Na                                  CN   CO     --         NHCO.sub.2 C.sub.2 H.sub.5                                                                OC.sub.2 H.sub.4                                                                        Na                                  CN   CO     --         CH.sub.3   NHC.sub.2 H.sub.4                                                                       Na                                  CO   SO.sub.2                                                                              NH.sub.2   OC.sub.6 H.sub.5                                                                          "        "                                   CO   SO.sub.2                                                                              CH.sub.3   OCH.sub.3  "        "                                   CN   SO.sub.2                                                                              --         C.sub.6 H.sub.5                                                                           "        "                                   CO   CO     CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2                                                                "        K                                     CO   CO     1,2-C.sub.6 H.sub.4 "        K                                     CO   CO     C.sub.2 H.sub.5                                                                           OC.sub.2 H.sub.5                                                                          "         K                                  CO   CO     CF.sub.3   H          "        K                                   CO   CO     OCH.sub.3  H          "        K                                   CO   CO     CH.sub.2 Cl                                                                               H          "        K                                   CO   CO     "          CH.sub.3   "        K                                   CO   CO     NHC.sub.2 H.sub.5                                                                         NH.sub.2   N(CH.sub.3)C.sub.2 H.sub.4                                                              K                                   CO   CO     NHC.sub.2 H.sub.5                                                                         NH.sub.2   N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                       K                                   CO   CO     OC.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                           NHC.sub.2 H.sub.4                                                                       K                                   CO   CO     OCH.sub.2C.sub.6 H.sub.5                                                                  "          NHC.sub.2 H.sub.4                                                                       K                                   CO   CO     OC.sub.6 H.sub.11                                                                         OCH.sub.3  NHC.sub.2 H.sub.4                                                                       K                                   CO   CO     C.sub.6 H.sub.5                                                                           OCH.sub.3  NHC.sub.2 H.sub.4                                                                       K                                   CO   CO     NHCOC.sub.2 H.sub.5                                                                       NHCO.sub.2 C.sub.2 H.sub.5                                                                NHC.sub.2 H.sub.4                                                                       K                                   CO   CO     NHSO.sub.2 C.sub.2 H.sub.5                                                                NHCO.sub.2 C.sub.2 H.sub.5                                                                NHC.sub.2 H.sub.4                                                                       K                                   CO   CO     NHCOC.sub.6 H.sub.5                                                                       NHCO.sub.2 C.sub.2 H.sub.5                                                                NHC.sub.2 H.sub.4                                                                       K                                   CO   CO     OC.sub.2 H.sub.5                                                                          NHCO.sub.2 C.sub.2 H.sub.5                                                                NHC.sub.2 H.sub.4                                                                       K                                   ______________________________________                                    

                  TABLE 8                                                          ______________________________________                                          ##STR22##                                                                     OH                                                                             Position                                                                              R.sup.2       X'Z              M                                        ______________________________________                                         2      5-CH.sub.3    NHC.sub.2 H.sub.4                                                                               Na                                       2      5-CH.sub.3    OC.sub.2 H.sub.4 Na                                       2      5-OCH.sub.3   NHC.sub.2 H.sub.4                                                                               K                                        2      5-Cl          "                Na                                       2      5-Cl          "                Na                                       4      3-OCH.sub.3   "                K                                        4      3-OCH.sub.3   "                K                                        3,4    H             "                Na                                       4      2-NHC.sub.6 H.sub.5                                                                          "                Na                                       2      5-NHCOCH.sub.3                                                                               "                Na                                       3,4    H             N(CH.sub.3)C.sub.2 H.sub.4                                                                      K                                                ##STR23##    NHC.sub.2 H.sub.4                                                                               K                                               C.sub.2 H.sub.4 OSO.sub.3 K                                             2      5-C.sub.6 H.sub.11                                                                           NHC.sub.2 H.sub.4                                                                               K                                        2      5-OC.sub.6 H.sub.5                                                                           N(C.sub.6 H.sub.5 )C.sub.2 H.sub.4                                                              "                                        2      5-SCH.sub.3   NHC.sub.2 H.sub.4                                                                               K                                        2      5-SC.sub.6 H.sub.5                                                                           NHCH.sub.2CH(C.sub.6 H.sub.5)                                                                   Na                                       2      5-NHCOOCH.sub.3                                                                              OC.sub.2 H.sub.4 Na                                       2      5-NHSO.sub.2 CH.sub.3                                                                        NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                              Na                                       2      5-NHCOCH.sub.3                                                                               NHC.sub.2 H.sub.4                                                                               NH.sub.4                                 2      5-NHCOCH.sub.2 Cl                                                                            OC.sub.2 H.sub.4 K                                        2      5-NHCOC.sub.2 H.sub.4 OH                                                                     OC.sub.2 H.sub.4 K                                        2      5-Cl          NHC.sub.3 H.sub.6                                                                               K                                        2      5-NHCONHC.sub.2 H.sub.5                                                                      OC.sub.2 H.sub.4 NH.sub.4                                 2      5-NHCON(C.sub.2 H.sub.5).sub.2                                                               NHC.sub.2 H.sub.4                                                                               K                                        2      5-CH.sub.3    "                "                                        2      5-NHCOCH.sub.3                                                                               "                "                                        4      H             "                Na                                       ______________________________________                                    

                                      TABLE 9                                      __________________________________________________________________________      ##STR24##                                                                     OH                                                                             Position                                                                            R.sup.2    R.sup.14                                                                               X'Z          M                                         __________________________________________________________________________     2    H          6-SO.sub.2 N(CH.sub.3).sub.2                                                           NHC.sub.2 H.sub.4                                                                           Na                                        2    H          "       "            "                                         2    3-CONH.sub.2                                                                              H       "            Na                                        4    H          H       N(CH.sub.3)C.sub.2 H.sub.4                                                                  "                                         4    H          H       OC.sub.2 H.sub.4                                                                            K                                         2,6  H          H       OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                           K                                         2    H          H       OC.sub.2 H.sub.4                                                                            K                                         "    H          6-SO.sub.2 NHCH.sub.3                                                                  OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                           K                                         2    3-CONH.sub.2                                                                              H       NHC.sub.2 H.sub.4                                                                           Na                                        2    3-CONHC.sub.6 H.sub.5                                                                     H       NHCH(C.sub. 2 H.sub.5)CH.sub.2                                                              Na                                        2    3-CONHC.sub.6 H.sub.4p                                                                    H       OC.sub.2 H.sub.4                                                                            NH.sub.4                                       OC.sub.2 H.sub.4 OH                                                       4    H          H       NHC.sub.2 H.sub.4                                                                           Na                                        4    H          H       NHC.sub.2 H.sub.4                                                                           Na                                        4    H          H       "            "                                         2    H          H       NHC.sub.2 H.sub.4                                                                           K                                         2    "          "       NHCH.sub.2CH(C.sub.6 H.sub.5)                                                               K                                         2    3-CO.sub.2 CH.sub.3                                                                       "       OC.sub.2 H.sub.4                                                                            Na                                        2    "          "       NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          Na                                        2,4  H          H       NHC.sub.2 H.sub.4                                                                           NH.sub.4                                  2    3-COCH.sub.2 Cl                                                                           "       OC.sub.2 H.sub.4                                                                            K                                         4    H          "       OC.sub.2 H.sub.4                                                                            K                                         4    H          H       NHC.sub.3 H.sub.6                                                                           K                                         4    H          "       OC.sub.2 H.sub.4                                                                            NH.sub.4                                  4    H          "       NHC.sub.2 H.sub.4                                                                           K                                         4    H          "       "            "                                         2    3-CONHC.sub.6 H.sub.5                                                                     "       "            "                                         2    H          "       N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                           "                                         __________________________________________________________________________

                                      TABLE 10                                     __________________________________________________________________________      ##STR25##                                                                     R.sup.16       R.sup.17                                                                            R.sup.2                                                                             R.sup.14                                                                            X'Z         M                                    __________________________________________________________________________     C.sub.6 H.sub.11                                                                              H    H    H    NHC.sub.2 H.sub.4                                                                          Na                                   C.sub.2 H.sub.4 CONH.sub.2                                                                    H    H    "    "           "                                    C.sub.2 H.sub.4 SO.sub.2 CHCH.sub.2                                                           H    H    8-OH "           Na                                   C.sub.2 H.sub.4 NHSO.sub.2 CH.sub.3                                                           H    H    H    N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                                     ##STR26##     H    3-OCH.sub.3                                                                         8-OH OC.sub.2 H.sub.4                                                                           K                                    C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                                                    H    H    H    OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          K                                    CH(CH.sub.3)C.sub.2 H.sub.5                                                                   H    H    H    OC.sub.2 H.sub.4                                                                           K                                    CH(CH.sub.3)CH.sub.2 CH(CH.sub.3)CH.sub.3                                                     CH.sub.3                                                                            H    H    OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          K                                    C.sub.6 H.sub.5                                                                               H    3-OCH.sub.3                                                                         H    NHC.sub.2 H.sub.4                                                                          Na                                   C.sub.2 H.sub.5                                                                               C.sub.2 H.sub.4 OH                                                                  "    H    NHCH(C.sub.2 H.sub.5)CH.sub.2                                                              Na                                   CH.sub.2 CH(OH)CH.sub.2 OH                                                                    "    H    H    OC.sub.2 H.sub.4                                                                           NH.sub.4                             C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                             H    H    H    NHC.sub.2 H.sub.4                                                                          Na                                   (CH.sub.2).sub.3 NHCOCH.sub.3                                                                 H    H    H    NHC.sub.2 H.sub.4                                                                          Na                                   C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                           H    H    H    "           "                                    C.sub.3 H.sub.6 OCH.sub.3                                                                     H    H    H    NHC.sub.2 H.sub.4                                                                          K                                    CH.sub.2 C.sub.6 H.sub.5                                                                      CH.sub.2 C.sub.6 H.sub.5                                                            "    "    NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                                    C.sub.6 H.sub.11                                                                              H    H    "    OC.sub.2 H.sub.4                                                                           Na                                   C.sub.2 H.sub.4 CONH.sub.2                                                                    H    "    "    NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                                   C.sub.2 H.sub.4 SO.sub.2 CHCH.sub.2                                                           H    H    8-OCH.sub.3                                                                         NHC.sub.2 H.sub.4                                                                          NH.sub.4                              ##STR27##     H    3-OC.sub.2 H.sub.5                                                                  8-OC.sub.2 H.sub.5                                                                  OC.sub.2 H.sub.4                                                                           K                                     ##STR28##     H    H    "    OC.sub.2 H.sub.4                                                                           K                                    C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                                                    H    H    H    NHC.sub.3 H.sub.6                                                                          K                                    CH(CH.sub.3)C.sub.2 H.sub.5                                                                   H    H    "    OC.sub.2 H.sub.4                                                                           NH.sub.4                             CH(CH.sub.3)CH.sub.2 CH(CH.sub.3)CH.sub.3                                                     H    H    "    NHC.sub.2 H.sub.4                                                                          K                                    C.sub.6 H.sub.5                                                                               H    3-C.sub.2 H.sub.5                                                                   "    "           "                                    C.sub.2 H.sub.5                                                                               "    H    "    "           "                                    CH.sub.2 CH(OH)CH.sub.2 OH                                                                    "    H    "    N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                                    __________________________________________________________________________

                                      TABLE 11                                     __________________________________________________________________________      ##STR29##                                                                     R.sup.2   R.sup.4 R.sup.5   X'Z            M                                   __________________________________________________________________________     H         C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 NHCOCH.sub.3                                                             NHC.sub.2 H.sub.4                                                                             Na                                  H         C.sub.2 H.sub.5                                                                        C.sub.3 H.sub.7n                                                                         N(CH.sub.3)C.sub.2 H.sub.4                                                                    "                                   H         "       C.sub.2 H.sub.5                                                                          NHCH.sub.2CH(OSO.sub.2 Na)CH.sub.2                                                            Na                                  H         CH.sub.3                                                                               C.sub.2 H.sub.4 SO.sub.2 CHCH.sub.2                                                      "              "                                   H         C.sub.2 H.sub.4 OH                                                                     C.sub.2 H.sub.4 CN                                                                       OC.sub.2 H.sub.4                                                                              K                                   3-CH.sub.3                                                                               C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 CN                                                                       OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                             Na                                  3-CH.sub.3                                                                               C.sub.2 H.sub.4 OH                                                                     C.sub. 2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                              Na                                  2-CH.sub.33-Cl                                                                           H       CH.sub.2 C.sub.6 H.sub.5                                                                 NHC.sub.3 H.sub.6                                                                             K                                   3-Cl      C.sub.6 H.sub.11                                                                       C.sub.2 H.sub.4 OSO.sub.3 K                                                              "              K                                   3-NHCOCH.sub.3                                                                           C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 CN                                                                       NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                            Na                                  "         "       C.sub.2 H.sub.4 CONH.sub.2                                                               NHC.sub.2 H.sub.4                                                                             K                                   2-CH.sub.3                                                                               H       C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                        NHC.sub.2 H.sub.4                                                                             Na                                  2-OC.sub.6 H.sub.5                                                                       C.sub.2 H.sub.4 CN                                                                     C.sub.2 H.sub.4 N(COCH.sub.3).sub.2                                                      N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                             "                                   3-SCH.sub.3                                                                              C.sub.2 H.sub.4 OCOCH.sub.3                                                            C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5                                               NHC.sub.2 H.sub.4                                                                             K                                   3-CH.sub.3                                                                               C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 OCOCH.sub.3                                                              NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                            Na                                  3-SC.sub.6 H.sub.5                                                                               C.sub.2 H.sub.4 SO.sub.2 NH(C.sub.2 H.sub.5)                                             NHCH.sub.2CH(C.sub.6 H.sub.5)                                                                 K                                   3-NHCOOCH.sub.3                                                                          C.sub.2 H.sub.4 OH                                                                     C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                              Na                                  3-NHSO.sub.2 CH.sub.3                                                                    C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 CN                                                                       NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                            Na                                  2-OCH.sub.3,                                                                             C.sub.2 H.sub.4 OCOCH.sub.3                                                            C.sub.2 H.sub.4 OCOCH.sub.3                                                              NHC.sub.2 H.sub.4                                                                             NH.sub.4                            5-NHCOCH.sub.3                                                                 3-NHCOCH.sub.2 Cl                                                                        C.sub.2 H.sub.4 OH                                                                     C.sub.6 H.sub.13                                                                         OC.sub.2 H.sub.4                                                                              K                                   3-NHCOC.sub.2 H.sub.4 OH                                                                 H       C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                              K                                   2-CH.sub.3, 3-Cl                                                                         H       CH.sub.2 C.sub.6 H.sub.5                                                                 NHC.sub.3 H.sub.6                                                                             K                                   2-NHCONHC.sub.2 H.sub.5                                                                  C.sub.2 H.sub.4 OH                                                                     C.sub.2 H.sub.4 CN                                                                       OC.sub.2 H.sub.4                                                                              NH.sub.4                            2-NHCON(C.sub.2 H.sub.5).sub.2                                                           C.sub.2 H.sub.4 OSO.sub.3 K                                                            C.sub.2 H.sub.5                                                                          NHC.sub.2 H.sub.4                                                                             K                                   3-CH.sub.3                                                                               C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "              "                                   3-NHCOCH.sub.3                                                                           "       C.sub.2 H.sub.4 CONH.sub.2                                                               "              "                                   H         "       C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "              Na                                  H         CH.sub.2 CH.sub.2OCH.sub.2 CH.sub.2                                                              "              Na                                  H         CH.sub.2 CH.sub.2SCH.sub.2 CH.sub. 2                                                             "              Na                                  H         CH.sub.2 CH.sub.2SO.sub.2CH.sub.2 CH.sub.2                                                       "              Na                                  H         CH.sub.2 CH.sub.2NHCH.sub.2 CH.sub.2                                                             "              Na                                  H         CH.sub.2 CH.sub.2NCOCH.sub.3CH.sub.2 CH.sub.2                                                    "              Na                                  __________________________________________________________________________

                                      TABLE 12                                     __________________________________________________________________________      ##STR30##                                                                     R.sup.2  R.sup.8 R.sup.4   X'Z         M                                       __________________________________________________________________________     7-CH.sub.3                                                                              2-CH.sub.3                                                                             C.sub.2 H.sub.5                                                                          NHC.sub.2 H.sub.4                                                                          K                                       "        "       "         N(C.sub.2 H.sub.5)C.sub.2 H.sub.4                                                          "                                       H        2,2,4-(CH.sub.3).sub.3                                                                 C.sub.2 H.sub.5                                                                          NHC.sub.3 H.sub.6                                                                          Na                                      H        "       C.sub.2 H.sub.4 OSO.sub.3 Na                                                             OC.sub.2 H.sub.4                                                                           Na                                      H        "       "         NHC.sub.2 H.sub.4                                                                          Na                                      7-CH.sub.3                                                                              2-CH.sub.3                                                                             C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "           "                                       7-NHCOCH.sub.3                                                                          H       C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           K                                       "        "       C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                         NHC.sub.2 H.sub.4                                                                          Na                                      5-CH.sub.3                                                                              "       "         "           K                                       8-CH.sub.3                                                                              "       C.sub.2 H.sub.4 OCH.sub.3                                                                N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          NH.sub.4                                7-CH.sub.3                                                                              2,2,4-(CH.sub.3).sub.3                                                                 C.sub.2 H.sub.5                                                                          NHC.sub.2 H.sub.4                                                                          K                                       "        "       C.sub.2 H.sub.4 Cl                                                                       NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         K                                       "        "       "         NHC.sub.2 H.sub.4                                                                          K                                       7-SC.sub.6 H.sub.5                                                                      "       C.sub.2 H.sub.4 SO.sub.2 NH(C.sub.2 H.sub.5)                                             NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                                       7-NHCOOCH.sub.3                                                                         CH.sub.3                                                                               C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           Na                                      7-NHSO.sub.2 CH.sub.3                                                                   2-C.sub.2 H.sub.5                                                                      C.sub.2 H.sub.4 CN                                                                       NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                                      7-OCH.sub.3,                                                                            3-OCOCH.sub.3                                                                          C.sub.2 H.sub.4 OCOCH.sub.3                                                              NHC.sub.2 H.sub.4                                                                          NH.sub.4                                5-NHCOCH.sub.3                                                                 7-NHCOCH.sub.2 Cl                                                                       3-OH    C.sub.6 H.sub.13                                                                         OC.sub.2 H.sub.4                                                                           K                                       7-NHCOC.sub.2 H.sub.4 OH                                                                3-CONH.sub.2                                                                           C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           K                                       7-CH.sub.3, 3-Cl                                                                        3-Cl    CH.sub.2 C.sub.6 H.sub.5                                                                 NHC.sub.3 H.sub.6                                                                          K                                       7-NHCONHC.sub.2 H.sub.5                                                                 3-OC.sub.6 H.sub.5                                                                     C.sub.2 H.sub.4 CN                                                                       OC.sub.2 H.sub.4                                                                           NH.sub.4                                7-NHCON(C.sub.2 H.sub.5)                                                                "       C.sub.2 H.sub.5                                                                          NHC.sub.2 H.sub.4                                                                          K                                       7-CH.sub.3                                                                              3-SC.sub.2 H.sub.5                                                                     C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "           "                                       7-NHCOCH.sub.3                                                                          3-CONHC.sub.2 H.sub.5                                                                  C.sub.2 H.sub.4 CONH.sub.2                                                               "           "                                       H        3-OCH.sub.3                                                                            C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "           Na                                      __________________________________________________________________________

                                      TABLE 13                                     __________________________________________________________________________      ##STR31##                                                                     R.sup.2    R.sup.8 R.sup.4  X'Z     M                                          __________________________________________________________________________     H          H       CH(CH.sub.3).sub.2                                                                      NHC.sub.2 H.sub.4                                                                      K                                          H          H       "        OC.sub.2 H.sub.4                                                                       K                                          6-CH.sub.3 3-CH.sub.3                                                                             C.sub.2 H.sub.5                                                                         "       Na                                         "          "       C.sub.2 H.sub.4 OH                                                                      "       "                                          "          "       C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                       NHC.sub.2 H.sub.4                                                                      Na                                         "          "       "        OC.sub.2 H.sub.4                                                                       K                                          "          "       C.sub.2 H.sub.4 OCH.sub.3                                                               NHC.sub.2 H.sub.4                                                                      K                                          6-NHCOCH.sub.3                                                                            H       C.sub.2 H.sub. 5                                                                        NHC.sub.3 H.sub.6                                                                      K                                          "          3-CH.sub.3                                                                             "        NHC.sub.2 H.sub.4                                                                      K                                          "          3-CH(CH.sub.3).sub.2                                                                   C.sub.2 H.sub.4 OCH.sub.3                                                               NHC.sub.2 H.sub.4                                                                      Na                                         "          "       C.sub.2 H.sub.4 OSO.sub.3 K                                                             N(CH.sub.3)C.sub.2 H.sub.4                                                             K                                          "          "       C.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                       K                                          "          "       C.sub.2 H.sub.4 OH                                                                      N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                      "                                          6-NHCOOCH.sub.3                                                                           2-CH.sub.2 OH                                                                          C.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                       Na                                         6-NHSO.sub.2 CH.sub.3                                                                     "       C.sub.2 H.sub.4 CN                                                                      NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                     Na                                         5-OCH.sub.3,                                                                              "       C.sub.2 H.sub.4 OCOCH.sub.3                                                             NHC.sub.2 H.sub.4                                                                      NH.sub.4                                   8-NHCOCH.sub.3                                                                 6-NHCOCH.sub.2 Cl                                                                         2-CH.sub.2 CH                                                                          C.sub.6 H.sub.13                                                                        OC.sub.2 H.sub.4                                                                       K                                          6-NHCOC.sub.2 H.sub.4 OH                                                                  H       C.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                       K                                          5-CH.sub.3, 8-Cl                                                                          2-CH.sub.2 Cl                                                                          CH.sub.2 C.sub.6 H.sub.5                                                                NHC.sub.3 H.sub.6                                                                      K                                          6-NHCONHC.sub.2 H.sub.5                                                                   2-CH.sub.2 Cl                                                                          C.sub.2 H.sub.4 CN                                                                      OC.sub.2 H.sub.4                                                                       NH.sub.4                                   6-NHCON(C.sub.2 H.sub.5).sub.2                                                            2-CH.sub.2 OC.sub.6 H.sub.5                                                            C.sub.2 H.sub.5                                                                         NHC.sub.2 H.sub.4                                                                      K                                          6-CH.sub.3 "       C.sub.2 H.sub.4 NHCOCH.sub.3                                                            "       "                                          6-NHCOCH.sub.3                                                                            2-C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                     C.sub.2 H.sub.4 CONH.sub.2                                                              "       "                                          H          "       C.sub.2 H.sub.4 NHCOCH.sub.3                                                            N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                      Na                                         __________________________________________________________________________

                                      TABLE 14                                     __________________________________________________________________________      ##STR32##                                                                     R.sup.9 R.sup.2   R.sup.4   X'Z         M                                      __________________________________________________________________________     C.sub.6 H.sub.5                                                                        H         H         NHC.sub.2 H.sub.4                                                                          Na                                     "       "         CH.sub.3  "           Na                                     CH.sub.3                                                                               "         C.sub.2 H.sub.4 OH                                                                       NHC.sub.2 H.sub.4                                                                          Na                                     CH.sub.3                                                                               "         "         OC.sub.2 H.sub.4                                                                           Na                                     "       5-CH.sub.3                                                                               "         NHC.sub.2 H.sub.4                                                                          K                                      C.sub.6 H.sub.5                                                                        5-Cl      H         "           "                                      C.sub.6 H.sub.5                                                                        5-NHCOCH.sub.3                                                                           C.sub.2 H.sub.4 CN                                                                       "           "                                      "       5-OCH.sub.3                                                                              CH.sub.3  "           "                                      "       H         "         "           Na                                     "       H         "         N(C.sub.2 H.sub.5)C.sub.2 H.sub.4                                                          Na                                     "       H         "         N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          Na                                     C.sub.6 H.sub.5                                                                        H         C.sub.2 H.sub.5                                                                          NHC.sub.2 H.sub.4                                                                          Na                                     C.sub.6 H.sub.5                                                                        H         CH.sub.3  NHC.sub.2 H.sub.4                                                                          Na                                     CH.sub.3                                                                               6-CH.sub.3                                                                               CH.sub.3  "           "                                      CF.sub.3                                                                               "         C.sub.6 H.sub.5                                                                          "           "                                      C.sub.6 H.sub.5                                                                        H         C.sub.2 H.sub.5                                                                          "           "                                      C.sub.6 H.sub.5                                                                        H         H         "           "                                      CONH.sub.2                                                                             "         CH.sub.3  "           "                                      CH.sub.3                                                                               "         CH.sub.3  N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                                      Cl      5-OC.sub.2 H.sub.5                                                                       "         NHC.sub.3 H.sub.6                                                                          "                                      CH.sub.3                                                                               "         H         NHC.sub.2 H.sub.4                                                                          "                                      C.sub.6 H.sub.4p-Br                                                                    H         H         "           "                                      C.sub.6 H.sub.5                                                                        "         C.sub.2 H.sub.4 CONH.sub.2                                                               "           K                                      C.sub.6 H.sub.4p-OCH.sub.3                                                             "         C.sub.2 H.sub.4 CN                                                                       N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          K                                      "       6-C.sub.6 H.sub.11                                                                       C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                        NHC.sub.2 H.sub.4                                                                          "                                      C.sub.2 H.sub.4 CN                                                                     4-OC.sub.6 H.sub.5                                                                       C.sub.2 H.sub.4 N(COCH.sub.3).sub.2                                                      "           "                                      C.sub.2 H.sub.4 OCOCH.sub.3                                                            5-SCH.sub.3                                                                              C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5                                               NHC.sub.2 H.sub.4                                                                          K                                      CH.sub.3                                                                               5-SC.sub.6 H.sub.5                                                                       C.sub.2 H.sub.4 SO.sub.2 NH(C.sub.2 H.sub.5)                                             NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                                      "       5-NHCOOCH.sub.3                                                                          C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           Na                                     C.sub.3 H.sub.7                                                                        6-NHSO.sub.2 CH.sub.3                                                                    C.sub.2 H.sub.4 CN                                                                       NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                                     CH.sub.3                                                                               6-OCH.sub.3,                                                                             C.sub.2 H.sub.4 OCOCH.sub.3                                                              NHC.sub.2 H.sub.4                                                                          NH.sub.4                                       5-NHCOCH.sub.3                                                         C.sub.2 H.sub.5                                                                        6-NHCOCH.sub.2 Cl                                                                        C.sub.6 H.sub.13                                                                         OC.sub.2 H.sub.4                                                                           K                                      OH      6-NHCOC.sub.2 H.sub.4 OH                                                                 C.sub.2 H.sub.4 OH                                                                       OC.sub.2 H.sub.4                                                                           K                                      SO.sub.2 NH.sub.2                                                                      "         CH.sub.2 C.sub.6 H.sub.5                                                                 NHC.sub.3 H.sub.6                                                                          K                                      SO.sub.2 NHC.sub.2 H.sub.5                                                             6-NHCONHC.sub.2 H.sub.5                                                                  C.sub. 2 H.sub.4 CN                                                                      OC.sub.2 H.sub.4                                                                           NH.sub.4                               OC.sub.6 H.sub.11                                                                      6-NHCON(C.sub.2 H.sub.5).sub.2                                                           C.sub.2 H.sub.5                                                                          NHC.sub.2 H.sub.4                                                                          K                                      SC.sub.2 H.sub.5                                                                       6-CH.sub.3                                                                               C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "           "                                      CONHC.sub.2 H.sub.5                                                                    6-NHCOCH.sub.3                                                                           C.sub.2 H.sub.4 CONH.sub.2                                                               "           "                                      OCH.sub.3                                                                              H         C.sub.2 H.sub.4 NHCOCH.sub.3                                                             "           Na                                     NHOCC.sub.2 H.sub.5                                                                    "         "         "           "                                      C.sub.6 H.sub.4p-CH.sub.3                                                              6-OH      "         "           "                                      __________________________________________________________________________

                  TABLE 15                                                         ______________________________________                                          ##STR33##                                                                     R.sup.9   R.sup.10    X'Z             M                                        ______________________________________                                         C.sub.6 H.sub.5                                                                          H           NHC.sub.2 H.sub.4                                                                              Na                                       "         H           NHCH[C(CH.sub.3).sub.3 ]CH.sub.2                                                               Na                                       "         H           OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                              Na                                       "         CH.sub.3    "               Na                                       CH.sub.3  C.sub.6 H.sub.5                                                                            "               Na                                       "         "           OC.sub.2 H.sub.4                                                                               Na                                       C.sub.6 H.sub.5                                                                          H           NHC.sub.2 H.sub.4                                                                              K                                        C.sub.6 H.sub.5                                                                          H           NHC.sub.2 H.sub.4                                                                              Na                                       "         H           "               "                                        "         H           "               "                                        "         CH.sub.3    "               "                                        "         H           "               "                                        "         "           N(CH.sub.3)C.sub.2 H.sub.4                                                                     "                                        "         "           N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                              "                                        C.sub.6 H.sub.5                                                                          H           NHC.sub.2 H.sub.4                                                                              Na                                       CH.sub.3  "           OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                              Na                                       CH.sub.3  H           OC.sub.2 H.sub.4                                                                               Na                                       CH.sub.3  C.sub.6 H.sub.5                                                                            NHC.sub.2 H.sub.4                                                                              Na                                       CH.sub.3  C.sub.6 H.sub.5                                                                            NHC.sub.3 H.sub.6                                                                              Na                                       C.sub.6 H.sub.5                                                                          CH.sub.3    NHC.sub.2 H.sub.4                                                                              Na                                       C.sub.6 H.sub.5                                                                          "           "               NH.sub.4                                 "         "           N(C.sub.2 H.sub.5)C.sub.2 H.sub.4                                                              "                                        CH.sub.3  H           NHC.sub.2 H.sub.4                                                                              K                                        "         H           NH(CH.sub.2).sub.5                                                                             K                                        C.sub.6 H.sub.4p-Br                                                                      "           OC.sub.2 H.sub.4                                                                               K                                        C.sub.6 H.sub.4p-OCH.sub.3                                                               "           OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                              K                                        "         Br          NHC.sub.2 H.sub.4                                                                              K                                        C.sub.2 H.sub.4 CN                                                                       "           N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                              K                                        C.sub.2 H.sub.4 OCOCH.sub.3                                                              "           NHC.sub.2 H.sub.4                                                                              K                                        CONH.sub.2                                                                               C.sub.2 H.sub.5                                                                            NHCH.sub.2CH(C.sub.6 H.sub.5)                                                                  K                                        SCN       C.sub.2 H.sub.5                                                                            OC.sub.2 H.sub.4                                                                               K                                        SO.sub.2 C.sub.2 H.sub.5                                                                 C.sub.6 H.sub.5                                                                            NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                             K                                        OCOCH.sub.3                                                                              C.sub.6 H.sub.4p-CH.sub.3                                                                  NHC.sub.2 H.sub.4                                                                              K                                        CONHC.sub.2 H.sub.5                                                                      "           OC.sub.2 H.sub.4                                                                               K                                        OH        H           OC.sub.2 H.sub.4                                                                               K                                        SO.sub.2 NH.sub.2                                                                        CONHC.sub.2 H.sub.5                                                                        NHC.sub.3 H.sub.6                                                                              K                                        SO.sub.2 NHC.sub.2 H.sub.5                                                               CH.sub.3    OC.sub.2 H.sub.4                                                                               K                                        OC.sub.6 H.sub.11                                                                        C.sub.2 H.sub.5                                                                            NHC.sub.2 H.sub.4                                                                              K                                        C.sub.2 H.sub.5                                                                          SCN         "               K                                        CONHC.sub.2 H.sub.5                                                                      CONH.sub.2  "               K                                        OCH.sub.3 CH(CH.sub.3).sub.2                                                                         "               K                                        NHOCC.sub.2 H.sub.5                                                                      C.sub.6 H.sub.5                                                                            "               K                                        "         C.sub.2 H.sub.5                                                                            "               K                                        ______________________________________                                    

                                      TABLE 16                                     __________________________________________________________________________      ##STR34##                                                                     R.sup.4  R.sup.11     X'Z          M                                           __________________________________________________________________________     H        CH.sub.3     NHC.sub.2 H.sub.4                                                                           K                                           H        C(CH.sub.3).sub.3                                                                           "            "                                           H        CF.sub.3     "            "                                           H        COOC.sub.2 H.sub.5                                                                          "            "                                           H        CONHC.sub.2 H.sub.4 OSO.sub.3 Na                                                            "            Na                                          H        C.sub.6 H.sub.5                                                                             "            K                                           C.sub.6 H.sub.5                                                                         CH.sub.3     "            "                                           "        C(CH.sub.3).sub.3                                                                           "            "                                           "        C.sub.6 H.sub.5                                                                             "            Na                                          "        C.sub.6 H.sub.5                                                                             "            "                                           C.sub.6 H.sub.5 SO.sub.2                                                                CH.sub.3     "            "                                           "        "            N(CH.sub.3)C.sub.2 H.sub.4                                                                  "                                           "        "            N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                           "                                           H        CH.sub.3     NHC.sub.2 H.sub.4                                                                           K                                           H        C.sub.6 H.sub.4p-OCH.sub.3                                                                  "            "                                           H        CF.sub.3     "            "                                           H        COOC.sub.2 H.sub.5                                                                          "            "                                                     ##STR35##   "            Na                                          H        C.sub.6 H.sub.5                                                                             "            K                                           C.sub.6 H.sub.5                                                                         C.sub.6 H.sub.4p-Br                                                                         "            "                                           "        C(CH.sub.3).sub.3                                                                           "            "                                           "        C.sub.6 H.sub.11                                                                            "            Na                                          "        C.sub.6 H.sub.5                                                                             "            Na                                          C.sub.6 H.sub.5 SO.sub.2                                                                CH.sub.3     N(CH.sub.3)C.sub.2 H.sub.4                                                                  Na                                          C.sub.2 H.sub.5 SO.sub.2                                                                "            NHC.sub.2 H.sub.4                                                                           K                                           CH.sub.3 CO                                                                             "            N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                           K                                           C.sub.6 H.sub.5 CO                                                                      CH.sub.3     NHC.sub.2 H.sub.4                                                                           K                                           CH.sub.3 CONH.sub.2   NHCH.sub.2CH(C.sub.6 H.sub.5)                                                               K                                           C.sub.2 H.sub.4 OH                                                                      C.sub.2 H.sub.5                                                                             OC.sub.2 H.sub.4                                                                            K                                           C.sub.2 H.sub.4 CN                                                                      "            NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          K                                           C.sub.2 H.sub.4 OCOCH.sub.3                                                             "            NHC.sub.2 H.sub.4                                                                           K                                           C.sub.6 H.sub.11                                                                        CF.sub.3     OC.sub.2 H.sub.4                                                                            K                                           C.sub.2 H.sub.4 OH                                                                      C.sub.6 H.sub.4p-Cl                                                                         OC.sub.2 H.sub.4                                                                            K                                           CH.sub.2 C.sub.6 H.sub.5                                                                CONHC.sub.2 H.sub. 5                                                                        NHC.sub.3 H.sub.6                                                                           K                                           C.sub.2 H.sub.4 CN                                                                      CH(CH.sub.3).sub.2                                                                          OC.sub.2 H.sub.4                                                                            K                                           C.sub.2 H.sub.5                                                                         "            NHC.sub.2 H.sub.4                                                                           K                                           C.sub.2 H.sub.4 NHCOCH.sub.3                                                            C.sub.2 H.sub.5                                                                             "            K                                           C.sub.2 H.sub.4 CONH.sub.2                                                              CH.sub.3     "            K                                           C.sub.2 H.sub.4 NHCOCH.sub.3                                                            C.sub.2 H.sub.5                                                                             "            K                                           "        C.sub.6 H.sub.5                                                                             "            K                                           __________________________________________________________________________

                                      TABLE 17                                     __________________________________________________________________________      ##STR36##                                                                     Q  Q'  R.sup.12    R.sup.13                                                                               X'Z     M                                           __________________________________________________________________________     CO CO  C.sub.6 H.sub.5                                                                            C.sub.6 H.sub.5                                                                        NHC.sub.2 H.sub.4                                                                      Na                                          CO CO  NH.sub.2    CH.sub. 3                                                                              "       "                                           CN CO   --         NHCO.sub.2 C.sub.2 H.sub.5                                                             OC.sub.2 H.sub.4                                                                       K                                           CN CO   --         CH.sub.2 OH                                                                            NHC.sub.2 H.sub.4                                                                      Na                                          CN CO   --         CH.sub.3                                                                               OC.sub.2 H.sub.4                                                                       Na                                          CO SO.sub.2                                                                           NH.sub.2    OC.sub.6 H.sub.5                                                                       NHC.sub.2 H.sub.4                                                                      Na                                          CO SO.sub.2                                                                           CH.sub.2 Cl OCH.sub.3                                                                              NHC.sub.2 H.sub.4                                                                      Na                                          CN SO.sub.2                                                                            --         C.sub.6 H.sub.5                                                                        NHC.sub.2 H.sub.4                                                                      Na                                          CO CO  CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2                                                                NHC.sub.2 H.sub.4                                                                      K                                           CO CO  1,2-C.sub.6 H.sub.4 NHC.sub.2 H.sub.4                                                                      K                                           CO CO  C.sub.2 H.sub.5                                                                            OC.sub.2 H.sub.5                                                                       NHC.sub.2 H.sub.4                                                                      K                                           CO CO  CH.sub.3    NH.sub.2                                                                               N(CH.sub.3)C.sub.2 H.sub.4                                                             K                                           CO CO  NHC.sub.2 H.sub.5                                                                          NH.sub.2                                                                               N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                      K                                           CO CO  NHC.sub.2 H.sub.5                                                                          CH.sub.3                                                                               OC.sub.2 H.sub.4                                                                       K                                           CO SO.sub.2                                                                           NH.sub.2    C.sub.2 H.sub.5                                                                        OC.sub.2 H.sub.4                                                                       K                                           CO CO  SC.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                        NHC.sub.2 H.sub.4                                                                      K                                           CO CO  SCH.sub.2C.sub.6 H.sub.5                                                                   C.sub.2 H.sub.5                                                                        NHC.sub.2 H.sub.4                                                                      K                                           CO CO  SC.sub.6 H.sub.11                                                                          OCH.sub.3                                                                              NHC.sub.2 H.sub.4                                                                      K                                           CO CO  C.sub.6 H.sub.5                                                                            OCH.sub.3                                                                              NHC.sub.2 H.sub.4                                                                      K                                           CO CO  NHCOC.sub.2 H.sub.5                                                                        NHCO.sub. 2 C.sub.2 H.sub.5                                                            NHC.sub.2 H.sub.4                                                                      K                                           CO CO  NHSO.sub.2 C.sub.2 H.sub.5                                                                 NHCO.sub.2 C.sub.2 H.sub.5                                                             NHC.sub.2 H.sub.4                                                                      K                                           CO CO  NHCOC.sub.6 H.sub.5                                                                        NHCO.sub.2 C.sub.2 H.sub.5                                                             NHC.sub.2 H.sub.4                                                                      K                                           CO CO  OC.sub.2 H.sub.5                                                                           NHCO.sub.2 C.sub.2 H.sub.5                                                             NHC.sub.2 H.sub.4                                                                      K                                           __________________________________________________________________________

                  TABLE 18                                                         ______________________________________                                          ##STR37##                                                                     OH                                                                             Position                                                                              R.sup.2        X'Z             M                                        ______________________________________                                         2      5-Cl           NHC.sub.2 H.sub.4                                                                              Na                                       2      5-Cl           NHC(CH.sub.3).sub.2 CH.sub.2                                                                   Na                                       2      5-OCH.sub.3    NHC(CH.sub.3).sub.2 CH.sub.2                                                                   Na                                       3,4    H              "               K                                        2      5-OCH.sub.3    "               Na                                       2      "              NHC.sub.2 H.sub.4                                                                              "                                        2      5-CH.sub.3     NHC.sub.2 H.sub.4                                                                              "                                        3,4    H              "               "                                        2      5-OCH.sub. 3   "               K                                        2      "              "               NH.sub.4                                 2      5-NHC.sub.6 H.sub.5                                                                           OC.sub.2 H.sub.4                                                                               Na                                       2      "              OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                              Na                                       2      5-NHCOCH.sub.3 NHC.sub.2 H.sub.4                                                                              Na                                       2      5-NHCOCH.sub.3 OC.sub.2 H.sub.4                                                                               Na                                       2      "              OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                              Na                                       2      "              N(CH.sub.3)C.sub. 2 H.sub.4                                                                    "                                        2      "              N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                              "                                        2      5-CH.sub. 3    NHC.sub.2 H.sub.4                                                                              Na                                       2      "              OC.sub.2 H.sub.4                                                                               Na                                       2      5-OCH.sub.3    NHC.sub.2 H.sub.4                                                                              K                                        2      5-Cl           "               Na                                       2      5-Cl           "               Na                                       4      2-OCH.sub.3    "               K                                        4      2-OCH.sub.3    "               K                                        3,4    H              "               Na                                       3,4    H              "               Na                                       2      3-NHCOCH.sub.3 "               Na                                       2      "              N(CH.sub.3)C.sub.2 H.sub.4                                                                     K                                                ##STR38##     NHC.sub.2 H.sub.4                                                                              K                                               C.sub.2 H.sub.4 OSO.sub.3 K                                             2      5-C.sub.6 H.sub.11                                                                            NHC.sub.2 H.sub.4                                                                              "                                        2      5-OC.sub.6 H.sub.5                                                                            N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                              "                                        2      5-SCH.sub.3    NHC.sub.2 H.sub.4                                                                              K                                        2      5-SC.sub.6 H.sub.5                                                                            NHCH.sub.2CH(C.sub.6 H.sub.5)                                                                  K                                        2      5-NHCOOCH.sub.3                                                                               OC.sub.2 H.sub.4                                                                               Na                                       2      5-NHSO.sub.2 CH.sub.3                                                                         NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                             Na                                       2      5-NCOCH.sub.3  NHC.sub.2 H.sub.4                                                                              NH.sub.4                                 2      5-NHCOCH.sub.2 Cl                                                                             OC.sub.2 H.sub.4                                                                               K                                        2      5-NHCOC.sub.2 H.sub.4 OH                                                                      OC.sub.2 H.sub.4                                                                               K                                        2      5-Cl           NHC.sub.3 H.sub.6                                                                              K                                        2      5-NHCONHC.sub.2 H.sub.5                                                                       OC.sub.2 H.sub.4                                                                               NH.sub.4                                 2      5-NHCON(C.sub.2 H.sub.5).sub.2                                                                NHC.sub.2 H.sub.4                                                                              K                                        2      5-CH.sub.3     "               "                                        2      5-NHCOCH.sub.3 "               "                                        4      H              "               Na                                       ______________________________________                                    

                                      TABLE 19                                     __________________________________________________________________________      ##STR39##                                                                     OH                                                                             Position                                                                            R.sup.2  R.sup.14   X'Z         M                                         __________________________________________________________________________     2    3-CO.sub.2 CH.sub.3                                                                     H          OC.sub.2 H.sub.4                                                                           K                                         4    H        H          "           "                                         4    H        H          "           "                                         4    H        H          NHC.sub.3 H.sub.6 OC.sub.2 H.sub.4                                                         Na                                        2    H        H          NHC.sub.2 H.sub.4                                                                          K                                         2    3-CONH.sub.2                                                                            H          "           K                                         2    3-CO.sub.2 CH.sub.3                                                                     H          OC.sub.2 H.sub.4                                                                           Na                                        2    H        6-SO.sub.2 N(CH.sub.3).sub.2                                                              NHC.sub.2 H.sub.4 NHC.sub.2 H.sub.4                                                        Na                                        2    "        6-SO.sub.2 NHC.sub.3 H.sub.6 OCH.sub.3                                                    OC.sub.2 H.sub.4                                                                           Na                                        2    "        6-SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                       OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          "                                         2    "        H          NHC.sub.2 H.sub.4                                                                          "                                         4    "        "          N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                                         2    "        "          N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                                         2    3-CONH.sub.2                                                                            H          NHC.sub.2 H.sub.4                                                                          K                                         2    "        "          NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                                         2    3-CO.sub.2 CH.sub.3                                                                     "          OC.sub.2 H.sub.4                                                                           Na                                        2    "        "          NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                                        2    H        "          NHC.sub.2 H.sub.4                                                                          NH.sub.4                                  2    3-CO.sub.2 CH.sub.2 Cl                                                                  "          OC.sub.2 H.sub.4                                                                           K                                         2    3-CO.sub.2 C.sub.2 H.sub.4 OH                                                           "          OC.sub.2 H.sub.4                                                                           K                                         4    H        H          NHC.sub.3 H.sub.6                                                                          K                                         2    3-CONHC.sub.2 H.sub.5                                                                   "          OC.sub.2 H.sub.4                                                                           NH.sub.4                                  2    3-CON(C.sub.2 H.sub.5).sub.2                                                            "          NHC.sub.2 H.sub.4                                                                          K                                         2    3-CO.sub.2 C.sub.2 H.sub.5                                                              "          "           "                                         2    3-CO.sub.2 CH(CH.sub.3).sub.2                                                           "          "           "                                         2    H        "          N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                                         __________________________________________________________________________

                                      TABLE 20                                     __________________________________________________________________________      ##STR40##                                                                     R.sup.16      R.sup.17 R.sup.2                                                                             R.sup.14                                                                            X'Z         M                                 __________________________________________________________________________     C.sub.6 H.sub.11                                                                             H        H    H    OC.sub.2 H.sub.4                                                                           K                                 C.sub.2 H.sub.4 CONH.sub.2                                                                   H        H    H    "           "                                 C.sub.2 H.sub.4 SO.sub.2 CHCH.sub.2                                                          H        H    8-OH "           "                                 C.sub.2 H.sub.4 NHSO.sub.2 CH.sub.3                                                          H        H    H    NHC.sub.3 H.sub.6 OC.sub.2 H.sub.4                                                         Na                                 ##STR41##    H        3-OCH.sub.3                                                                         8-OH NHC.sub.2 H.sub.4                                                                          K                                 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub. 3                                                  H        H    H    "           K                                 CH(CH.sub.3)C.sub.2 H.sub.5                                                                  H        H    H    OC.sub.2 H.sub.4                                                                           Na                                CH(CH.sub.3)CH.sub.2 CH(CH.sub.3)CH.sub.3                                                    H        H    H    NHC.sub.2 H.sub.4 NHC.sub.2 H.sub.4                                                        Na                                C.sub.6 H.sub.5                                                                              C.sub.2 H.sub.4 OH                                                                      2-OCH.sub.3                                                                         H    OC.sub.2 H.sub.4                                                                           Na                                C.sub.2 H.sub.5                                                                              H        "    H    OC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                          "                                 CH.sub.2 CH(OH)CH.sub.2 OH                                                                   H        "    H    NHC.sub.2 H.sub.4                                                                          "                                 C.sub.2 H.sub.4 SO.sub.2 NH.sub.2                                                            H        "    "    N(CH.sub.3)C.sub.2 H.sub.4                                                                 "                                 (CH.sub.2).sub.6 NHCOCH.sub.3                                                                H        "    "    N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                                 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OH                                                          H        H    H    NHC.sub.2 H.sub.4                                                                          K                                 CH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.2 C.sub.6 H.sub.5                                                                "    "    NHCH.sub.2CH(C.sub.6 H.sub.5)                                                              K                                 CH.sub.3      H        H    "    OC.sub.2 H.sub.4                                                                           Na                                C.sub.6 H.sub.11                                                                             H        "    "    NHC.sub.2 H.sub.4 OC.sub.2 H.sub.4                                                         Na                                C.sub.2 H.sub.4 CONH.sub.2                                                                   H        H    "    NHC.sub.2 H.sub.4                                                                          NH.sub.4                          C.sub.2 H.sub.4 SO.sub.2 CHCH.sub.2                                                          H        H    8-OCH.sub.3                                                                         OC.sub.2 H.sub.4                                                                           K                                  ##STR42##    H        3-OC.sub.2 H.sub.5                                                                  8-OC.sub.2 H.sub.5                                                                  OC.sub.2 H.sub.4                                                                           K                                  ##STR43##    H        H    H    NHC.sub.3 H.sub.6                                                                          K                                 C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                                                   CH.sub.3 H    "    OC.sub.2 H.sub.4                                                                           NH.sub.4                          CH(CH.sub.3)C.sub.2 H.sub.5                                                                  CH.sub.3 H    "    NHC.sub.2 H.sub.4                                                                          K                                 CH(CH.sub.3)CH.sub.2 CH(CH.sub.3)CH.sub.3                                                    CH.sub.3 3-C.sub.2 H.sub.5                                                                   "    "           "                                 C.sub.6 H.sub.5                                                                              CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                      H    "    "           "                                 C.sub.2 H.sub.5                                                                              "        H    "    N(C.sub.6 H.sub.5)C.sub.2 H.sub.4                                                          "                                 __________________________________________________________________________

The invention has been described in detail with particular reference to certain preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope of the invention. 

We claim:
 1. A dye of the formula: ##STR44## and wherein C is a coupler selected from ##STR45## wherein R² and R¹⁴ each represents up to three groups selected from hydrogen, fluorine, chlorine, bromine, alkyl, cycloalkyl, alkoxy, phenoxy, alkylthio, arylthio, and radicals having the formula --NH--X--R³ in which X is --CO--, --COO--, or --SO₂ -- and R³ is selected from alkyl and alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy, and when X is --CO--, R³ also is selected from hydrogen, amino, alkylamino, dialkylamino, arylamino, aryl, and furyl;R⁴ and R⁵ are each selected from hydrogen, alkyl, aryl, cycloalkyl, and alkyl substituted with halogen, CN, OH, alkoxy, aryloxy, alkoxyalkoxy, alkanoyl, alkanoyloxy, carbamoyl, alkylcarbamoyl, sulfamoyl, alkylsulfamoyl, alkoxyalkanoyloxy, and cycloalkyl, and R⁴ and R⁵ together represent a single, combined group --CH₂ CH₂ CH₂ CH₂ CH₂ --, --CH₂ CH₂ OCH₂ CH₂ --, --CH₂ CH₂ --S--CH₂ CH₂ --, or --CH₂ CH₂ --SO₂ --CH₂ CH₂ --; R⁸ represents one or two groups each selected from hydrogen, alkyl and alkyl substituted with --CN, alkoxy, alkoxycarbonyl, alkoxycarbonyloxy, phenyl, cyclohexoxy, --OH, --Cl and Br; R⁹, R¹⁰ and R¹¹ are each selected from hydrogen, alkyl, phenyl, or phenyl substituted with 1-3 groups selected from Cl, Br, alkyl or alkoxy, alkylthio, benzylthio, cyclohexylthio and phenylthio; Q and Q' are each selected from --CO--, --SO₂ --, or --CN; R¹² and R¹³ are each selected from alkyl, hydroxyalkyl, alkoxy, alkoxycarbonylamino, trifluoromethyl, phenyl or phenyl substituted with 1-3 groups selected from Cl, Br, alkyl or alkoxy, alkoxycarbonylalkyl, cyanoalkyl, amino, haloalkyl, alkylamino, alkylthio, benzylthio, cyclohexylthio and phenylthio; and R¹² and R¹³ together comprise --CH₂ C(CH₃)₂ CH₂ --, or 1,2--C₆ H₄ -- connecting Q and Q'; R¹⁶ and R¹⁷ are selected from hydrogen, cycloalkyl, aryl, alkyl, and alkyl substituted with alkoxy, hydroxy, alkoxyalkoxy, hydroxyalkoxy, carbamoyl, sulfamoyl, alkanoylamino, or alkenylsulfonyl, and aryl substituted with hydroxyalkyl; e is 1 or 2; t and t' are each 1 or zero; X' is O, NH, N(alkyl)--, or N(aryl)--; Z is selected from straight- or branched-chain alkylene, and such alkylene substituted with phenyl, halogen, OSO₃ M, alkoxy or aryloxy groups, --CH₂ (CH₂)_(m) V--CH₂ (CH₂)_(p) --, where m is 1, 2 or 3, p is 0, 1, 2 or 3, and V is O, S, SO₂, --SO₂ NH--, --SO₂ N(alkyl)--, --SO₂ N(aryl), --N(SO₂ aryl)--, --NH, --NHCO--, -- NHCONH, --N(SO₂ alkyl), or --CON(alkyl); M is H, Na, K or NH₄ ; n is 1 or 2; and wherein each of the above alkyl and alkoxy groups contain from 0 to three of the following: hydroxy; halogen; cyano; succinimido; glutarimido; phthalimido; 2-pyrrolidino; cyclohexyl; phenyl or phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl; alkanoylamino; sulfamoyl; alkylsulfamoyl; vinylsulfonyl; acrylamido; phthalimidinyl; benzoylsulfonicimidyl; alkylsulfonamido; phenylsulfonamido; alkoxycarbonylamino; alkylcarbamoyloxy; alkoxycarbonyl; alkoxycarbonyloxy; ##STR46## wherein Y is --NH--, --NH--alkyl--, --O--, --S--, or --CH₂ O--; --S--R⁶, wherein R⁶ is alkyl, phenyl, phenyl substituted with halogen, alkyl, alkoxy, alkanoylamino, cyano, or alkoxycarbonyl, pyridyl, pyrimidinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, or ##STR47## --SO₂ R³ ; --COOR³ ; --OXR³ ; --NH--X--R³ ; --X--R³ ; --SO₂ NR⁷ R⁷ ; wherein R³ and X are as defined above and each R⁷ is selected from H and R³ ; alkoxy; alkoxy substituted with hydroxy, cyano, alkanoyloxy, or alkoxy; phenoxy; or phenoxy substituted with one or more of alkyl, alkoxy or halogen.
 2. The dye according to claim 1 of the formula ##STR48##
 3. The dye according to claim 1 of the formula ##STR49##
 4. The dye according to claim 1 of the formula ##STR50## 